Partially fluorinated alkanols having a tertiary structure

ABSTRACT

Novel partially fluorinated alkanes having the Formula:  &lt;IMAGE&gt; wherein each R is the same or different and is selected from the group consisting of CF3, CHF2, CH2F, and CH3CF2, and R&#39; is an alkyl or fluoroalkyl group having 1 to 6 carbon atoms have utility as solvents in a variety of industrial cleaning applications including cold cleaning, dry cleaning, and defluxing of printed circuit boards.

This application is a division of application Ser. No. 625,727, filed Dec. 4, 1990, now abandoned.

FIELD OF THE INVENTION

This invention relates to novel partially fluorinated alkanols having a tertiary structure and 4 to 9 carbon atoms. These compounds are useful in a variety of vapor degreasing, cold cleaning, and solvent cleaning applications including defluxing and dry cleaning.

BACKGROUND OF THE INVENTION

Cold cleaning is an application where numerous solvents are used. In most cold cleaning applications, the soiled part is either immersed in the fluid or wiped with rags or similar objects soaked in solvents and allowed to air dry.

In cold cleaning applications, the use of the aerosol packaging concept has long been found to be a convenient and cost effective means of dispensing solvents. Aerosol products utilize a propellant gas or mixture of propellant gases, preferably in a liquefied gas rather than a compressed gas state, to generate sufficient pressure to expel the active ingredients, i.e. product concentrates such as solvents, from the container upon opening of the aerosol valve. The propellants may be in direct contact with the solvent, as in most conventional aerosol systems, or may be isolated from the solvent, as in barrier-type aerosol systems.

Vapor degreasing and solvent cleaning with fluorocarbon based solvents have found widespread use in industry for the degreasing and otherwise cleaning of solid surfaces, especially intricate parts and difficult to remove soils.

In its simplest form, vapor degreasing or solvent cleaning consists of exposing a room temperature object to be cleaned to the vapors of a boiling solvent. Vapors condensing on the object provide clean distilled solvent to wash away grease or other contamination. Final evaporation of solvent from the object leaves behind no residue as would be the case where the object is simply washed in liquid solvent.

For soils which are difficult to remove, where elevated temperature is necessary to improve the cleaning action of the solvent, or for large volume assembly line operations where the cleaning of metal parts and assemblies must be done efficiently and quickly, the conventional operation of a vapor degreaser consists of immersing the part to be cleaned in a sump of boiling solvent which removes the bulk of the soil, thereafter immersing the part in a sump containing freshly distilled solvent near room temperature, and finally exposing the part to solvent vapors over the boiling sump which condense on the cleaned part. In addition, the part can also be sprayed with distilled solvent before final rinsing.

Vapor degreasers suitable in the above-described operations are well known in the art. For example, Sherliker et al. in U.S. Pat. No. 3,085,918 disclose such suitable vapor degreasers comprising a boiling sump, a clean sump, a water separator, and other ancillary equipment.

Chlorofluorocarbon solvents, such as trichlorotrifluoroethane, have attained widespread use in recent years as effective, nontoxic, and nonflammable agents useful in degreasing applications and other solvent cleaning applications. One isomer of trichlorotrifluoroethane is 1,1,2-trichloro-1,2,2-trifluoroethane (known in the art as CFC-113). CFC-113 has a boiling point of about 47° C. and has been found to have satisfactory solvent power for greases, oils, waxes and the like. It has therefore found widespread use for cleaning electric motors, compressors, heavy metal parts, delicate precision metal parts, printed circuit boards, gyroscopes, guidance systems, aerospace and missile hardware, aluminum parts and the like.

Another commonly used solvent is chloroform (known in the art as HCC-20) which has a boiling point of about 63° C. Perchloroethylene is a commonly used dry cleaning and vapor degreasing solvent which has a boiling point of about 121° C. These compounds are disadvantageous for use as solvents because they are toxic; also, chloroform causes liver damage when inhaled in excess.

Although chlorine is known to contribute to the solvency capability of a compound, fully halogenated chlorofluorocarbons and hydrochlorocarbons are suspected of causing environmental problems in connection with the earth's protective ozone layer. Thus, the art is seeking new compounds which do not contribute to environmental problems but yet provide the solvency properties of CFC-113. From an environmental standpoint, partially fluorinated alkanols are of interest because they are considered to be stratospherically safe substitutes for the currently used fully halogenated chlorofluorocarbons.

It is an object of this invention to provide novel partially fluorinated alkanols which are liquid at room temperature and which are useful as solvents for use in vapor degreasing, cold cleaning, and other solvent cleaning applications including defluxing applications and dry cleaning.

Another object of the invention is to Provide novel environmentally acceptable solvents for use in the aforementioned applications.

Other objects and advantages of the invention will become apparent from the following description.

DETAILED DESCRIPTION OF THE INVENTION

We have found a novel class of alkanols which we believe have good solvency characteristics. The present novel compounds are of the Formula: ##STR2## wherein each R is the same or different and is selected from the group consisting of CF₃, CHF₂, CH₂ F, and CH₃ CF₂ --, and R' is an alkyl or fluoroalkyl group having 1 to 6 carbon atoms.

Because C in the Formula above has three alkyl groups thereon, these novel compounds have a tertiary structure. We believe that this tertiary structure provides good solvency power. When the present compounds are used as solvents, the compounds have good solvency power for polar contaminants such as polyols and amines and for nonpolar contaminants including hydrocarbons such as mineral oil. We also believe that these novel compounds have boiling points which are comparable to those of currently used solvents.

Preferably, R' in the Formula above is selected the group consisting of CF₃, CHF₂, CH₂ F, CH₃, CF₃ CF₂ --, CF₃ (CF₂)₂ --, CF₃ CF₂ CHF--, CF₃ CF₂ CH₂ --, CF₃ CHF--, CF₃ (CHF)₂ --, CF₃ CHFCF₂ --, CF₃ CHFCH₂ --, CF₃ CH₂ --, CF₃ (CH₂)₂ --, CF₃ CH₂ CF₂ --, CF₃ CH₂ CHF--, CHF₂ CF₂ --, CHF₂ (CF₂)₂ --, CHF₂ CF₂ CHF--, CHF₂ CF₂ CH₂ --, CHF₂ CHF--, CHF₂ (CHF)₂ --, CHF₂ CHFCF₂ --, CHF₂ CHFCH₂ --, CHF₂ CH₂ --, CHF₂ (CH₂)₂ --, CHF₂ CH₂ CF₂ --, CHF₂ CH₂ CHF--, CH₂ FCF₂ --, CH₂ F(CF₂)₂ --, CH₂ FCF₂ CHF-- , CH₂ FCF₂ CH₂ --, CH₂ FCHF--, CH₂ F(CHF)₂ --, CH₂ FCHFCF₂ --, CH₂ FCHFCH₂ --, CH₂ FCH₂ --, CH₂ F(CH₂)₂ --, CH₂ FCH₂ CF₂ --, CH₂ FCH₂ CHF--, CH₃ CF₂ --, CH₃ (CF₂)₂ --, CH₃ CF₂ CHF--, CH₃ CF₂ CH₂ --, CH₃ CHF--, CH₃ (CHF)₂ --, CH₃ CHFCF₂ --, CH₃ CHFCH₂ --, CH₃ CH₂ --, CH₃ (CH₂)₂ --, CH₃ (CH₂)₃ --, CH₃ CH₂ CF₂ --, CH₃ (CH₂)₂ CF₂ --, CH₃ (CH₂)₃ CF₂ --, CH₃ CH₂ (CF₂)₂ --, CH₃ (CH₂)₂ (CF₂)₂ --, and CH₃ (CH₂)₃ (CF₂)₂ --.

In the Formula above, when one R is CF₃, the other R is CHF₂, and R' is CH₃, the compound is 2-methyl-1,1,1,3,3-pentafluoro-2-propanol. When one R is CF₃, the other R is CHF₂, and R' is CF₃ CF₂ --, the compound is 2-difluoromethyl-1,1,1,3,3,4,4,4-octafluoro-2-butanol. When one R is CF₃, the other R is CHF₂, and R' is CH₃ CF₂ --, the compound is 2-difluoromethyl-1,1,1,3,3-pentafluoro-2-butanol. When one R is CF₃, the other R is CHF₂, and R' is CH₃ (CF₂)₂ --, the compound is 2-difluoromethyl-1,1,1,3,3,4,4-heptafluoro-2-pentanol. When one R is CF₃, the other R is CHF₂, and R' is CH₃ CH₂ CF₂ --, the compound is 2-difluoromethyl-1,1,1,3,3-pentafluoro-2-pentanol. When one R is CF₃, the other R is CHF₂, and R' is CH₃ CH₂ (CF₂ )₂ --, the compound is 2-difluoromethyl-1,1,1,3,3,4,4-heptafluoro-2-hexanol.

When one R is CF₃, the other R is CH₂ F, and R' is CH₃, the compound is 2-methyl-1,1,1,3-tetrafluoro-2-propanol. When one R is CF₃, the other R is CH₂ F, and R' is CHF₂ CHF--, the compound is 2-fluoromethyl-1,1,1,3,4,4-hexafluoro-2-butanol. When one R is CF₃, the other R is CH₂ F, and R' is CH₃ CF₂ --, the compound is 2-fluoromethyl-1,1,1,3,3-pentafluoro-2-butanol. When one R is CF₃, the other R is CH₂ F, and R' is CH₃ (CF₂)₂ --, the compound is 2fluoromethyl-1,1,1,3,3,4,4-heptafluoro-2-pentanol. When one R is CF₃, the other R is CH₂ F, and R' is CH₃ CH₂ CF₂ --, the compound is 2-fluoromethyl-1,1,1,3,3-pentafluoro-2-pentanol. When one R is CF₃, the other R is CH₂ F, and R' is CH₃ CH₂ (CF₂)₂ --, the compound is 2-fluoromethyl-1,1,1,3,3,4,4-heptafluoro-2-hexanol.

When one R is CF₃, the other R is CH₃ CF₂ --, and R' is CH₃, the compound is 2-methyl-1,1,1,3,3-pentafluoro-2-butanol. When one R is CHF₂, the other R is CH₂ F, and R' is CH₃, the compound is 2-methyl-1,1,3-trifluoro-2-propanol.

It is believed that the present novel compounds may be prepared by adapting known methods for preparing known alkanols coupled with the knowledge of one skilled in the art. For example, 2-methyl-1,1,1,3,3-pentafluoro-2-propanol may be prepared by reacting commercially available 1,1,1-trifluoro-2-propanone with CF₂ carbene to form 2-trifluoromethyl-1,1-difluoro-1-propene which may then be reacted with sulfuric acid and then water to form 2-methyl-1,1,1,3,3-pentafluoro-2-propanol.

To prepare 2-difluoromethyl-1,1,1,3,3,4,4,4-octafluoro-2-butanol, caesium fluoride and perfluoro-3-methylbut-1-ene may be reacted in moist sulpholan as taught by Robert N. Haszeldine et al., "Fluoro-olefin Chemistry. Part 11. Some Reactions of Perfluoro-3-methylbut-1-ene under Ionic and Free-radical Conditions", J. Chem. Soc. 565 (1979) to form 2-trifluoromethyl-1,1,1,3,3,4,4,4-octafluorobutane. The 2-trifluoromethyl-1,1,1,3,3,4,4,4-octafluorobutane may then be dehydrohalogenated and then reacted with sulfuric acid and then water to form 2-difluoromethyl-1,1,1,3,3,4,4,4-octafluoro-2-butanol.

As another example, 2-difluoromethyl-1,1,1,3,3-pentafluoro-2-butanol may be prepared by fluorinating commercially available 2-butanone to form 2,2-difluorobutane which may then be dehydrogenated to form 3,3-difluoro-1-butene. CF₃ may then be added to the 3,3-difluoro-1-butene to form 2-trifluoromethyl-1,3,3-trifluorobutane which may then be dehydrogenated to form 2-trifluoromethyl-1,3,3-trifluoro-1-butene. The 2-trifluoromethyl-1,3,3-trifluoro-1-butene may then be reacted with hydrogen fluoride to form 2-difluoromethyl-1,1,1,3,3,3-hexafluorobutane which may then be dehydrogenated to form 2-trifluoromethyl-1,1,3,3-tetrafluoro-1-butene which may then be reacted with sulfuric acid and then water to form 2-difluoromethyl-1,1,1,3,3-pentafluoro-2-butanol.

As another example, 2-difluoromethyl-1,1,1,3,3,4,4-heptafluoro-2-pentanol may be prepared by fluorinating commercially available 2,3-pentanedione to form 2,2,3,3-tetrafluoropentane which may then be dehydrogenated to form 3,3,4,4-tetrafluoro-1-pentene. CF₃ may then be added to the 3,3,4,4-tetrafluoro-1-pentene to form 2-trifluoromethyl-1,3,3,4,4-pentafluoropentane which may then be dehydrogenated to form 2-trifluoromethyl-1,3,3,4,4-pentafluoro-1-pentene. The 2-trifluoromethyl-1,3,3,4,4-pentafluoro-1-pentene may then be reacted with hydrogen fluoride to form 2-trifluoromethyl-1,1,3,3,4,4-hexafluoropentane which may then be dehydrogenated to form 2-trifluoromethyl-1,1,3,3,4,4-hexafluoro-1-pentene which may then be reacted with sulfuric acid and then water to form 2-difluoromethyl-1,1,1,3,3,4,4-heptafluoro-2-pentanol.

As another example, 2-difluoromethyl-1,1,1,3,3-pentafluoro-2-pentanol may be prepared by fluorinating commercially available 3-pentanone to form 3,3-difluoropentane which may then be dehydrogenated to form 3,3-difluoro-1-pentene. CF₃ may then be reacted with the 3,3-difluoro-1-pentene to form 2-trifluoromethyl-1,3,3-trifluoropentane which may then be dehydrogenated to form 2-trifluoromethyl-1,3,3-trifluoro-1-pentene. The 2-trifluoromethyl-1,3,3-trifluoro-1-pentene may then be reacted with hydrogen fluoride to form 2-trifluoromethyl-1,1,3,3-tetrafluoropentane which may then be dehydrogenated to form 2-trifluoromethyl-1,1,3,3-tetrafluoro-1-pentene which may then be reacted with sulfuric acid and then water to form 2-difluoromethyl-1,1,1,3,3-pentafluoro-2-pentanol.

As another example, 2-difluoromethyl-1,1,1,3,3,4,4-heptafluoro-2-hexanol may be prepared by fluorinating commercially available 3,4-hexanedione to form 3,3,4,4-tetrafluorohexane which may then be dehydrogenated to form 3,3,4,4-tetrafluoro-1-hexene. CF₃ may then be added to the 3,3,4,4-tetrafluoro-1-hexene to form 2-trifluoromethyl-1,3,3,4,4-pentafluorohexane which may then be dehydrogenated to form 2-trifluoromethyl-1,3,3,4,4-pentafluoro-1-hexene. The 2-trifluoromethyl-1,3,3,4,4-pentafluoro-1-hexene may then be reacted with hydrogen fluoride to form 2-trifluoromethyl-1,1,3,3,4,4-hexafluorohexane which may then be dehydrogenated to form 2-trifluoromethyl-1,1,3,3,4,4-hexafluoro-1-hexene which may then be reacted with sulfuric acid and then water to form 2-difluoromethyl-1,1,1,3,3,4,4-heptafluoro-2-hexanol.

As another example, 2-methyl-1,1,1,3-tetrafluoro-2-propanol may be prepared by reacting commercially available methacrylic acid with hydrogen fluoride to form 2-methyl-3-fluoropropanoic acid which may then be fluorinated to form 2-methyl-1,1,1,3-tetrafluoropropane. The 2-methyl-1,1,1,3-tetrafluoropropane may then be dehydrogenated and reacted with sulfuric acid and then water to form 2-methyl-1,1,1,3-tetrafluoro-2-propanol.

As another example, 2-fluoromethyl-1,1,1,3,4,4-hexafluoro-2-butanol may be prepared by fluorinating commercially available 3-chloropropionic acid to form 1,1,1,3-tetrafluoropropane which may then be reacted with CHF₂ CF carbene to form 2-fluoromethyl-1,1,1,3,4,4-hexafluorobutane. The 2-fluoromethyl-1,1,1,3,4,4-hexafluorobutane may then be dehydrogenated and reacted with sulfuric acid and then water to form 2-fluoromethyl-1,1,1,3,4,4-hexafluoro-2-butanol.

As another example, 2-fluoromethyl-1,1,1,3,3-pentafluoro-2-butanol may be prepared by fluorinating commercially available 2-butanone to form 2,2-difluorobutane which may then be dehydrogenated to form 3,3-difluoro-1-butene. CF₃ may then be added to the 3,3-difluoro-1-butene to form 2-trifluoromethyl-1,3,3-trifluorobutane which may then be dehydrogenated to form 2-trifluoromethyl-1,3,3-trifluoro-1-butene. The 2-trifluoromethyl-1,3,3-trifluoro-1-butene may then be reacted with sulfuric acid and then water to form 2-fluoromethyl-1,1,1,3,3-pentafluoro-2-butanol.

As another example, 2-fluoromethyl-1,1,1,3,3,4,4-heptafluoro-2-pentanol may be prepared by fluorinating commercially available 2,3-pentanedione to form 2,2,3,3-tetrafluoropentane which may then be dehydrogenated to form 3,3,4,4-tetrafluoro-1-pentene. CF₃ may then be added to the 3,3,4,4-tetrafluoro-1-pentene to form 2-trifluoromethyl-1,3,3,4,4-pentafluoropentane which may then be dehydrogenated to form 2-trifluoromethyl-1,3,3,4,4-pentafluoro-1-pentene. The 2-trifluoromethyl-1,3,3,4,4-pentafluoro-1-pentene may then be reacted with sulfuric acid and then water to form 2-fluoromethyl-1,1,1,3,3,4,4-heptafluoro-2-pentanol.

As another example, 2-fluoromethyl-1,1,1,3,3-pentafluoro-2-pentanol may be prepared by fluorinating 3-pentanone to form 3,3-difluoropentane which may then be dehydrogenated to form 3,3-difluoro-1-pentene. CF₃ may then be reacted with the 3,3-difluoro-1-pentene to form 2-trifluoromethyl-1,3,3-trifluoropentane which may then be dehydrogenated to form 2-trifluoromethyl-1,3,3-trifluoro-1-pentene. The 2-trifluoromethyl-1,3,3-trifluoro-1-pentene may then be reacted with sulfuric acid and then water to form 2-fluoromethyl-1,1,1,3,3-pentafluoro-2-pentanol.

As another example, 2-fluoromethyl-1,1,1,3,3,4,4-heptafluoro-2-hexanol may be prepared by fluorinating commercially available 3,4-hexanedione to form 3,3,4,4-tetrafluorohexane which may then be dehydrogenated to form 3,3,4,4-tetrafluoro-1-hexene. CF₃ may then be added to the 3,3,4,4-tetrafluoro-1-hexene to form 2-trifluoromethyl-1,3,3,4,4-pentafluorohexane which may then be dehydrogenated to form 2-trifluoromethyl-1,3,3,4,4-pentafluoro-1-hexene. The 2-trifluoromethyl-1,3,3,4,4-pentafluoro-1-hexene may then be reacted with sulfuric acid and then water to form 2-fluoromethyl-1,1,1,3,3,4,4-heptafluoro-2-hexanol.

As another example, 2-methyl-1,1,1,3,3-pentafluoro-2-butanol may be prepared by fluorinating commercially available 2-methyl-1-buten-3-yne to form 2-methyl-1,2,3,4-tetrafluoro-1-butene which may then be reacted with hydrogen fluoride to form 2-methyl-1,2,3,3,4-pentafluorobutane. The 2-methyl-1,2,3,3,4-pentafluorobutane may then be dehalogenated to form 3-methyl-2,3,4-trifluoro-1-butene which may then be reacted with hydrogen fluoride to form 2-methyl-1,2,3,3-tetrafluorobutane. The 2-methyl-1,2,3,3-tetrafluorobutane may then be dehalogenated to form 2-methyl-1,3,3-trifluoro-1-butene which may then be fluorinated to form 2-methyl-1,1,2,3,3-pentafluorobutane. The 2-methyl-1,1,2,3,3-pentafluorobutane may then be dehydrohalogenated to form 2-methyl-1,1,3,3-tetrafluoro-1-butene which may then be reacted with hydrogen fluoride to form 2-methyl-1,1,1,3,3-pentafluorobutane. The 2-methyl-1,1,1,3,3-pentafluorobutane may then be dehydrogenated and then reacted with sulfuric acid and water to form 2-methyl-1,1,1,3,3-pentafluoro-2-butanol.

As another example, 2-methyl-1,1,3-trifluoro-2-propanol may be prepared by reacting commercially available fluoroacetone with a CF₂ carbene to form 2-methyl-1,1,3-trifluoro-1-propene which may then be reacted with sulfuric acid and then water to form 2-methyl-1,1,3-trifluoro-2-propanol.

Preferably, each R in the Formula above is the same. When each R is CHF₂ and R' is CF₃, the compound is 2-difluoromethyl-1,1,1,3,3-pentafluoro-2-propanol. When each R is CHF₂ and R' is CHF₂, the compound is 2-difluoromethyl-1,1,3,3-tetrafluoro-2-propanol. When each R is CHF₂ and R' is CH₂ F, the compound is 2-fluoromethyl-1,1,3,3-tetrafluoro-2-propanol. When each R is CHF₂ and R' is CH₃, the compound is 2-methyl-1,1,3,3-tetrafluoro-2-propanol. When each R is CH₂ F and R' is CHF₂, the compound is 2-fluoromethyl-1,1,3-trifluoro-2-propanol. When each R is CH₂ F and R' is CH₂ F, the compound is 2-fluoromethyl-1,3-difluoro-2-propanol.

As another preparation example, 2-difluoromethyl-1,1,1,3,3-pentafluoro-2-propanol may be prepared by fluorinating commercially available 1,1,1,3,3-pentachloro-2-propanone to form 1,1,1,3,3-pentafluoro-2-propanone which may then be reacted with CF₂ carbene to form 2-difluoromethyl-1,1,3,3,3-tetrafluoro-1-propene. The 2-difluoromethyl-1,1,3,3,3-tetrafluoro-1-propene may then be reacted with sulfuric acid and then water to form 2-difluoromethyl-1,1,1,3,3-pentafluoro-2-propanol.

As another example, the 2-difluoromethyl-1,1,3,3-tetrafluoro-2-propanol may be prepared by fluorinating commercially available 1,1,3-trichloro-2-propanone to form 1,1,3-trifluoro-2-propanone which may then be reacted with CF₂ carbene to form 2-fluoromethyl-1,1,3,3-tetrafluoro-1-propene. The 2-fluoromethyl-1,1,3,3-tetrafluoro-1-propene may then be hydrogenated to form 2-fluoromethyl-1,1,3,3-tetrafluoropropane. The 2-fluoromethyl-1,1,3,3-tetrafluoropropane may then be dehydrogenated to form 2-difluoromethyl-1,3,3-trifluoro-1-propene which may then be reacted with hydrogen fluoride to form 2-difluoromethyl-1,1,3,3-tetrafluoropropane. The 2-difluoromethyl-1,1,3,3-tetrafluoropropane may then be dehydrogenated and then reacted with sulfuric acid and then water to form 2-difluoromethyl-1,1,3,3-tetrafluoro-2-propanol.

As another example, 2-fluoromethyl-1,1,3,3-tetrafluoro-2-propanol may be prepared by fluorinating commercially available 1,1,3-trichloro-2-propanone to form 1,1,3-trifluoro-2-propanone which may then be reacted with CF₂ carbene to form 2-fluoromethyl-1,1,3,3-tetrafluoro-1-propene. The 2-fluoromethyl-1,1,3,3-tetrafluoro-1-propene may then be reacted with sulfuric acid and then water to form 2-fluoromethyl-1,1,3,3-tetrafluoro-2-propanol.

As another example, 2-methyl-1,1,3,3-tetrafluoro-2-propanol may be prepared by fluorinating commercially available 1,1-dichloro-2-propanone to form 1,1-difluoro-2-propanone which may then be reacted with CF₂ carbene to form 2-methyl-1,1,3,3-tetrafluoro-1-propene. The 2-methyl-1,1,3,3-tetrafluoro-1-propene may then be reacted with sulfuric acid and then water to form 2-methyl-1,1,3,3-tetrafluoro-2-propanol.

As another example, the 2-fluoromethyl-1,1,3-trifluoro-2-propanol may be prepared by oxidizing commercially available 1,3-difluoro-2-propanol to 1,3-difluoro-2-propanone which may then be reacted with a CF₂ carbene to form 2-fluoromethyl-1,1,3-trifluoro-1-propene. The 2-fluoromethyl-1,1,3-trifluoro-1-propene may then be reacted with sulfuric acid and then water to form 2-fluoromethyl-1,1,3-trifluoro-2-propanol.

As another example, the 2-fluoromethyl-1,3-difluoro-2-propanol may be prepared by oxidizing commercially available 1,3-difluoro-2-propanol to 1,3-difluoro-2-propanone which may then be reacted with a CF₂ carbene to form 2-fluoromethyl-1,1,3-trifluoro-1-propene. The 2-fluoromethyl-1,1,3-trifluoro-1-propene may then be hydrogenated to form 2-fluoromethyl-1,1,3-trifluoropropane. The 2-fluoromethyl-1,1,3-trifluoropropane may then be dehydrohalogenated to form 2-fluoromethyl-1,3-difluoro-1-propene which may then be reacted with sulfuric acid and then water to form 2-fluoromethyl-1,3-difluoro-2-Propanol.

More preferably, each R in the Formula above is CF₃. When R is CF₃ CF₂ CHF--, the compound is 2-trifluoromethyl-1,1,1,3,4,4,5,5,5-nonafluoro-2-pentanol. To prepare 2-trifluoromethyl-1,1,1,3,4,4,5,5,5-nonafluoro-2-pentanol, commercially available hexafluoropropene may be oligomerized with commercially available trimethylamine in a dipolar aprotic solvent such as commercially available tetrahydrofuran to provide (CF₃)₂ C:CFCF₂ CF₃ as taught by W. Brunskill et al., "Anionic Oligomerisation of Hexafluoropropene: Fission of a Carbon-Carbon Bond by Fluoride Ion", Chemical Communications, 1444 (1970); the (CF₃)₂ C:CFCF₂ CF₃ may then be reacted with sulfuric acid and then water to form 2-trifluoromethyl-1,1,1,3,4,4,5,5,5-nonafluoro-2-pentanol.

Most preferably, each R is CF₃ and R' is selected from the group consisting of CHF₂, CH₃, CF₃ CF₂ CHF--, CF₃ CHF--, CF₃ CH₂ --, CHF₂ CH₂ --, CH₃ CF₂ --, CH₃ CH₂ CF₂ --, CH₃ (CH₂)₂ CF₂ --, CH₃ CH₂ --, and CH₃ (CH₂)₂ --. The names of the preceding preferred hydrofluorocarbons are 2-difluoromethyl-1,1,1,3,3,3-hexafluoro-2-propanol; 2-methyl-1,1,1,3,3,3-hexafluoro-2-propanol; 2-trifluoromethyl-1,1,1,3,4,4,5,5,5-nonafluoro-2-pentanol; 2-trifluoromethyl-1,1,1,3,4,4,4-heptafluoro-2-butanol: 2-trifluoromethyl-1,1,1,4,4,4-hexafluoro-2-butanol; 2-trifluoromethyl-1,1,1,4,4-pentafluoro-2-butanol; 2-trifluoromethyl-1,1,1,3,3-pentafluoro-2-butanol; 2-trifluoromethyl-1,1,1,3,3-pentafluoro-2-pentanol: 2-trifluoromethyl-1,1,1,3,3-pentafluoro-2-hexanol; 2-trifluoromethyl-1,1,1-trifluoro-2-butanol; and 2-trifluoromethyl-1,1,1-trifluoro-2-pentanol.

As another example, 2-difluoromethyl-1,1,1,3,3,3-hexafluoro-2-propanol may be prepared by treating commercially available hexafluoropropene with hydrogen fluoride as taught by commonly assigned U.K. Patent 902,590 to form 1,1,1,2,3,3,3-heptafluoropropane. The 1,1,1,2,3,3,3-heptafluoropropane may then be heated at 475°-700° C. in the presence of activated carbon as taught by commonly assigned U.S. Pat. No. 2,981,763 which is incorporated herein by reference to form 2-trifluoromethyl-1,1,1,3,3,3-hexafluoropropane or nonafluoroisobutane. The nonafluoroisobutane may then be treated with commercially available benzoyl chloride in the presence of commercially available triethylamine as taught by B. L. Dyatkin et al., "The Perfluoro-t-butyl Anion in the Synthesis of Organofluorine Compounds", Russian Chemical Reviews 45(7). 607 (1976) to form perfluoroisobutene. The perfluoroisobutene may then be reacted with sulfuric acid and then water to form 2-difluoromethyl-1,1,1,3,3,3-hexafluoro-2-propanol.

As another example, 2-methyl-1,1,1,3,3,3-hexafluoro-2-propanol may be prepared by reacting commercially available hexafluoropropene with elemental sulfur and commercially available potassium fluoride in commercially available dimethylformamide under substantially atmospheric pressure and at temperatures between 25°-100° C. as taught by commonly assigned U.S. Pat. No. 4,326,068 which is incorporated herein by reference to form hexafluorothioacetone dimer. The hexafluorothioacetone dimer may then be reacted with commercially available formaldehyde as taught by commonly assigned U.S. Pat. No. 4,367,349 which is incorporated herein by reference to form hexafluoroisobutylene. The hexafluoroisobutylene may then be reacted with sulfuric acid and then water to form 2-methyl-1,1,1,3,3,3-hexafluoro-2-propanol.

To prepare 2-trifluoromethyl-1,1,1,3,4,4,5,5,5-nonafluoro-2-pentanol, commercially available hexafluoropropene may be oligomerized with commercially available trimethylamine in a dipolar aprotic solvent such as commercially available tetrahydrofuran to provide (CF₃)₂ C:CFCF₂ CF₃ which is then reacted with commercially available hydrogen fluoride to yield 2-trifluoromethyl-1,1,1,3,3,4,4,5,5,5-decafluoropentane as taught by W. Brunskill et al., "Anionic Oligomerisation of Hexafluoropropene: Fission of a Carbon-Carbon Bond by Fluoride Ion", Chemical Communications, 1444 (1970). The 2-trifluoromethyl-1,1,1,3,3,4,4,5,5,5-decafluoropentane may then be dehydrohalogenated and then reacted with sulfuric acid and then water to form 2-trifluoromethyl-1,1,1,3,4,4,5,5,5-nonafluoro-2-pentanol.

As another example, 2-trifluoromethyl-1,1,1,3,4,4,4-heptafluoro-2-butanol may be prepared by reacting commercially available 1,1-difluoroethylene according to the procedure of George L. Fleming et al., "Addition of Free Radicals to Unsaturated Systems. Part XX. The Direction of Radical Addition of Heptafluoro-2-iodopropane to Vinyl Fluoride, Trifluoroethylene, and Hexafluoropropene", J. C. S. Perkin I, 574 (1973) to form a product which may then be fluorinated to form 2-trifluoromethyl-1,1,1,2,3,4,4,4-octafluorobutane. The 2-trifluoromethyl-1,1,1,2,3,4,4,4-octafluorobutane may then be dehydrohalogenated and then reacted with sulfuric acid and then water to form 2-trifluoromethyl-1,1,1,3,4,4,4-heptafluoro-2-butanol.

As another example, 2-trifluoromethyl-1,1,1,4,4,4-hexafluoro-2-butanol may be prepared by reacting commercially available 1,1-difluoroethylene according to the procedure of George L. Fleming et al., supra, to form a product which may then be reacted with hydrogen fluoride to form 2-trifluoromethyl-1,1,1,2,4,4,4-hexafluorobutane which may then be dehydrohalogenated and then reacted with sulfuric acid and then water to form 2-trifluoromethyl-1,1,1,4,4,4-hexafluoro-2-butanol.

As another example, 2-trifluoromethyl-1,1,1,4,4-pentafluoro-2-butanol may be prepared by reacting commercially available 1,1-difluoroethylene according to the procedure of George L. Fleming et al., supra, to form a product which may then be hydrogenated to form 2-trifluoromethyl-1,1,1,2,4,4-hexafluorobutane which may then be dehydrohalogenated and then reacted with sulfuric acid and then water to form 2-trifluoromethyl-1,1,1,4,4-pentafluoro-2-butanol.

As another example, 2-trifluoromethyl-1,1,1,3,3-pentafluoro-2-butanol may be prepared by fluorinating commercially available 2-butanone to form 2,2-difluorobutane which may then be dehydrogenated to form 3,3-difluoro-1-butene. CF₃ may then be added to the 3,3-difluoro-1-butene to form 2-trifluoromethyl-1,3,3-trifluorobutane which may then be dehydrogenated to form 2-trifluoromethyl-1,3,3-trifluoro-1-butene. The 2-trifluoromethyl-1,3,3-trifluoro-1-butene may then be reacted with hydrogen fluoride to form 2-difluoromethyl-1,1,1,3,3-pentafluorobutane which may then be dehydrogenated to form 2-trifluoromethyl-1,1,3,3-tetrafluoro-1-butene which may then be fluorinated to form 2-trifluoromethyl-1,1,1,2,3,3-hexafluorobutane. The 2-trifluoromethyl-1,1,1,2,3,3-hexafluorobutane is then hydrolyzed to form 2-trifluoromethyl-1,1,1,3,3-pentafluoro-2-butanol.

As another example, 2-trifluoromethyl-1,1,1,3,3-pentafluoro-2-pentanol may be prepared by fluorinating commercially available 3-pentanone to form 3,3-difluoropentane which may then be dehydrogenated to form 3,3-difluoro-1-pentene. CF₃ may then be reacted with the 3,3-difluoro-1-pentene to form 2-trifluoromethyl-1,3,3-trifluoropentane which may then be dehydrogenated to form 2-trifluoromethyl-1,3,3-trifluoro-1-pentene. The 2-trifluoromethyl-1,3,3-trifluoro-1-pentene may then be reacted with hydrogen fluoride to form 2-trifluoromethyl-1,1,3,3-tetrafluoropentane which may then be dehydrogenated to form 2-trifluoromethyl-1,1,3,3-tetrafluoro-1-pentene which may then be fluorinated to form 2-trifluoromethyl-1,1,1,2,3,3-hexafluoropentane. The 2-trifluoromethyl-1,1,1,2,3,3-hexafluoropentane is then hydrolyzed to form 2-trifluoromethyl-1,1,1,3,3-pentafluoro-2-pentanol.

As another example, 2-trifluoromethyl-1,1,1,3,3-pentafluoro-2-hexanol may be prepared by fluorinating commercially available 3-hexanone to form 3,3-difluorohexane which may then be dehydrogenated to form 3,3-difluoro-2-hexene. CF₃ may then be reacted with the 3,3-difluoro-2-hexene to form 2-trifluoromethyl-1,3,3-trifluorohexane which may then be dehydrogenated to form 2-trifluoromethyl-1,3,3-trifluoro-1-hexene. The 2-trifluoromethyl-1,3,3-trifluoro-1-hexene may then be reacted with hydrogen fluoride to form 2-trifluoromethyl-1,1,3,3-tetrafluorohexane which may then be dehydrogenated to form 2-trifluoromethyl-1,1,3,3-tetrafluoro-1-hexene which may then be fluorinated to form 2-trifluoromethyl-1,1,1,2,3,3-hexafluorohexane. The 2-trifluoromethyl-1,1,1,2,3,3-hexafluorohexane may then be hydrolyzed to form 2-trifluoromethyl-1,1,1,3,3-pentafluoro-2-hexanol.

As another example, 2-trifluoromethyl-1,1,1-trifluoro-2-butanol may be prepared by fluorinating commercially available butyraldehyde to form 1,1-difluorobutane which may then be dehydrogenated to form 1,1-difluoro-1-butene. CF₃ may then be reacted with the 1,1-difluoro-1-butene to form 2-trifluoromethyl-1,1,1-trifluorobutane which may then be dehydrogenated to form 2-trifluoromethyl-1,1,1-trifluoro-2-butene. The 2-trifluoromethyl-1,1,1-trifluoro-2-butene may then be reacted with water to form 2-trifluoromethyl-1,1,1-trifluoro-2-butanol.

As another example, 2-trifluoromethyl-1,1,1-trifluoro-2-pentanol may be prepared by fluorinating commercially available 2-pentenal to form 1,1,2,3-tetrafluoropentane which may then be dehydrogenated to form 1,1-difluoro-1-pentene. CF₃ may then be reacted with the 1,1-difluoro-1-pentene to form 2-trifluoromethyl-1,1,1-trifluoropentane which may then be dehydrogenated to form 2-trifluoromethyl-1,1,1-trifluoro-2-pentene. The 2-trifluoromethyl-1,1,1-trifluoro-2-pentene may then be reacted with water to form 2-trifluoromethyl-1,1,1-trifluoro-2-pentanol.

The present compounds are useful as solvents for use in vapor degreasing and other solvent cleaning applications including defluxing, cold cleaning, dry cleaning, dewatering, decontamination, spot cleaning, aerosol propelled rework, extraction, particle removal, and surfactant cleaning applications. These compounds are also useful as blowing agents, Rankine cycle and absorption refrigerants, and power fluids and especially as refrigerants for centrifugal refrigeration chillers.

The present invention also provides a method of cleaning a solid surface which comprises treating the surface with a compound having the Formula: ##STR3## wherein each R is the same or different and is selected from the group consisting of CF₃, CHF₂, CH₂ F, and CH₃ CF₂, and R' is an alkyl or fluoroalkyl group having 1 to 6 carbon atoms.

Preferably, R' in the Formula above is selected from the group consisting of CF₃, CHF₂, CH₂ F, CH₃, CF₃ CF₂ --, CF₃ (CF₂)₂ --, CF₃ CF₂ CHF--, CF₃ CF₂ CH₂ --, CF₃ CHF--, CF₃ (CHF)₂ --, CF₃ CHFCF₂ --, CF₃ CHFCH₂ --, CF₃ CH₂ --, CF₃ (CH₂)₂ --, CF₃ CH₂ CF₂ --, CF₃ CH₂ CHF--, CHF₂ CF₂ --, CHF₂ (CF₂)₂ --, CHF₂ CF₂ CHF--, CHF₂ CF₂ CH₂ --, CHF₂ CHF--, CHF₂ (CHF)₂ --, CHF₂ CHFCF₂ --, CHF₂ CHFCH₂ --, CHF₂ CH₂ --, CHF₂ (CH₂)₂ --, CHF₂ CH₂ CF₂ --, CHF₂ CH₂ CHF--, CH₂ FCF₂ --, CH₂ F(CF₂)₂ --, CH₂ FCF.sub. 2 CHF--, CH₂ FCF₂ CH₂ --, CH₂ FCHF--, CH₂ F(CHF)₂ --, CH₂ FCHFCF₂ --, CH₂ FCHFCH₂ --, CH₂ FCH₂ --, CH₂ F(CH₂)₂ --, CH₂ FCH₂ CF₂ --, CH₂ FCH₂ CHF--, CH₃ CF₂ --, CH₃ (CF₂)₂ --, CH₃ CF₂ CHF--, CH₃ CF₂ CH₂ --, CH₃ CHF--, CH₃ (CHF)₂ --, CH₃ CHFCF₂ --, CH₃ CHFCH₂ --, CH₃ CH₂ --, CH₃ (CH₂)₂ --, CH₃ (CH₂)₃ --, CH₃ CH₂ CF₂ --, CH₃ (CH₂)₂ CF₂ --, CH₃ (CH₂)₃ CF₂ --, CH₃ CH₂ (CF₂)₂ --, CH₃ (CH₂)₂ (CF₂)₂ --, and CH₃ (CH₂)₃ (CF₂)₂ --.

In the process embodiment of the invention, the compositions may be used to clean solid surfaces by treating the surfaces with the compounds in any manner well known to the art such as by dipping or spraying or use of conventional degreasing apparatus.

When the novel compounds are used to clean solid surfaces by spraying the surfaces with the compounds, preferably, the novel compounds are sprayed onto the surfaces by using a propellant. Preferably, the propellant is selected from the group consisting of hydrochlorofluorocarbon, hydrofluorocarbon, and mixtures thereof. Useful hydrochlorofluorocarbon propellants include dichlorofluoromethane (known in the art as HCFC-21), chlorodifluoromethane (known in the art as HCFC-22), 1,1-dichloro-2,2-difluoroethane (known in the art as HCFC-132a), 1-chloro-2,2,2-trifluoroethane (known in the art as HCFC-133), and 1-chloro-1,1-difluoroethane (known in the art as HCFC-142b); commercially available HCFC-21, HCFC-22, and HCFC-142b may be used in the present invention. Useful hydrofluorocarbon propellants include trifluoromethane (known in the art as HFC-23), 1,1,1,2-tetrafluoroethane (known in the art as HFC-134a), and 1,1-difluoroethane (known in the art as HFC-152a): commercially available HFC-23 and HFC-152a may be used in the present invention. Until HFC-134a becomes available in commercial quantities, HFC-134a may be made by a known method such as that disclosed by U.S. Pat. No. 4,851,595. Preferred propellants include chlorodifluoromethane and 1,1,1,2-tetrafluoroethane. The present invention is more fully illustrated by the following non-limiting Examples.

EXAMPLES 1-573

For each example, the novel compound of the Formula above having the R and R' groups as indicated in Table I below is made.

                  TABLE I                                                          ______________________________________                                         Example  R               R"                                                    ______________________________________                                          1       CF.sub.3, CHF.sub.2                                                                            CF.sub.3                                               2       CF.sub.3, CHF.sub.2                                                                            CHF.sub.2                                              3       CF.sub.3, CHF.sub.2                                                                            CH.sub.2 F                                             4       CF.sub.3, CHF.sub.2                                                                            CH.sub.3                                               5       CF.sub.3, CHF.sub.2                                                                            CF.sub.3 CF.sub.2                                      6       CF.sub.3, CHF.sub.2                                                                            CF.sub.3 (CF.sub.2).sub.2                              7       CF.sub.3, CHF.sub.2                                                                            CF.sub.3 CF.sub.2 CHF                                  8       CF.sub.3, CHF.sub.2                                                                            CF.sub.3 CF.sub.2 CH.sub.2                             9       CF.sub.3, CHF.sub.2                                                                            CF.sub.3 CHF                                           10      CF.sub.3, CHF.sub.2                                                                            CF.sub.3 (CHF).sub.2                                   11      CF.sub.3, CHF.sub.2                                                                            CF.sub.3 CHFCF.sub.2                                   12      CF.sub.3, CHF.sub.2                                                                            CF.sub.3 CHFCH.sub.2                                   13      CF.sub.3, CHF.sub.2                                                                            CF.sub.3 CH.sub.2                                      14      CF.sub.3, CHF.sub.2                                                                            CF.sub.3 (CH.sub.2).sub.2                              15      CF.sub.3, CHF.sub.2                                                                            CF.sub.3 CH.sub.2 CF.sub.2                             16      CF.sub.3, CHF.sub.2                                                                            CF.sub.3 CH.sub.2 CHF                                  17      CF.sub.3, CHF.sub.2                                                                            CHF.sub.2 CF.sub.2                                     18      CF.sub.3, CHF.sub.2                                                                            CHF.sub.2 (CF.sub.2).sub.2                             19      CF.sub.3, CHF.sub.2                                                                            CHF.sub.2 CF.sub.2 CHF                                 20      CF.sub.3, CHF.sub.2                                                                            CHF.sub.2 CF.sub.2 CH.sub.2                            21      CF.sub.3, CHF.sub.2                                                                            CHF.sub.2 CHF                                          22      CF.sub.3, CHF.sub.2                                                                            CHF.sub.2 (CHF).sub.2                                  23      CF.sub.3, CHF.sub.2                                                                            CHF.sub.2 CHFCF.sub.2                                  24      CF.sub.3, CHF.sub.2                                                                            CHF.sub.2 CHFCH.sub.2                                  25      CF.sub.3, CHF.sub.2                                                                            CHF.sub.2 CH.sub.2                                     26      CF.sub.3, CHF.sub.2                                                                            CHF.sub.2 (CH.sub.2).sub.2                             27      CF.sub.3, CHF.sub.2                                                                            CHF.sub.2 CH.sub.2 CF.sub.2                            28      CF.sub.3, CHF.sub.2                                                                            CHF.sub.2 CH.sub.2 CHF                                 29      CF.sub.3, CHF.sub.2                                                                            CH.sub.2 FCF.sub.2                                     30      CF.sub.3, CHF.sub.2                                                                            CH.sub.2 F(CF.sub.2).sub.2                             31      CF.sub.3, CHF.sub.2                                                                            CH.sub.2 FCF.sub.2 CHF                                 32      CF.sub.3, CHF.sub.2                                                                            CH.sub.2 FCF.sub.2 CH.sub.2                            33      CF.sub.3, CHF.sub.2                                                                            CH.sub.2 FCHF                                          34      CF.sub.3, CHF.sub.2                                                                            CH.sub.2 (CHF).sub.2                                   35      CF.sub.3, CHF.sub.2                                                                            CH.sub.2 FCHFCF.sub.2                                  36      CF.sub.3, CHF.sub.2                                                                            CH.sub.2 FCHFCH.sub.2                                  37      CF.sub.3, CHF.sub.2                                                                            CH.sub.2 FCH.sub.2                                     38      CF.sub.3, CHF.sub.2                                                                            CH.sub.2 F(CH.sub.2).sub.2                             39      CF.sub.3, CHF.sub.2                                                                            CH.sub.2 FCH.sub.2 CF.sub.2                            40      CF.sub.3, CHF.sub.2                                                                            CH.sub.2 FCH.sub.2 CHF                                 41      CF.sub.3, CHF.sub.2                                                                            CH.sub.3 CF.sub.2                                      42      CF.sub.3, CHF.sub.2                                                                            CH.sub.3 (CF.sub.2).sub.2                              43      CF.sub.3, CHF.sub.2                                                                            CH.sub.3 CF.sub.2 CHF                                  44      CF.sub.3, CHF.sub.2                                                                            CH.sub.3 CF.sub.2 CH.sub.2                             45      CF.sub.3, CHF.sub.2                                                                            CH.sub.3 CHF                                           46      CF.sub.3, CHF.sub.2                                                                            CH.sub.3 (CHF).sub.2                                   47      CF.sub.3, CHF.sub.2                                                                            CH.sub.3 CHFCF.sub.2                                   48      CF.sub.3, CHF.sub.2                                                                            CH.sub.3 CHFCH.sub.2                                   49      CF.sub.3, CHF.sub.2                                                                            CH.sub.3 CH.sub.2 CF.sub.2                             50      CF.sub.3, CHF.sub.2                                                                            CH.sub.3 CH.sub.2 (CF.sub.2).sub.2                     51      CF.sub.3, CHF.sub.2                                                                            CH.sub.3 (CH.sub.2)CF.sub.2 CF.sub.2                   52      CF.sub.3, CHF.sub.2                                                                            CH.sub.3 (CH.sub.2).sub.2 (CF.sub.2).sub.2             53      CF.sub.3, CHF.sub.2                                                                            CH.sub.3 (CH.sub.2).sub.3 CF.sub.2                     54      CF.sub.3, CHF.sub.2                                                                            CH.sub.3 (CH.sub.2).sub.3 (CF.sub.2).sub.2             55      CF.sub.3, CH.sub.2 F                                                                           CF.sub.3                                               56      CF.sub.3, CH.sub.2 F                                                                           CHF.sub.2                                              57      CF.sub.3, CH.sub.2 F                                                                           CH.sub.2 F                                             58      CF.sub.3, CH.sub.2 F                                                                           CH.sub.3                                               59      CF.sub. 3, CH.sub.2 F                                                                          CF.sub.3 CF.sub.2                                      60      CF.sub.3, CH.sub.2 F                                                                           CF.sub.3 (CF.sub.2).sub.2                              61      CF.sub.3, CH.sub.2 F                                                                           CF.sub.3 CF.sub.2 CHF                                  62      CF.sub.3, CH.sub.2 F                                                                           CF.sub.3 CF.sub.2 CH.sub.2                             63      CF.sub.3, CH.sub.2 F                                                                           CF.sub.3 CHF                                           64      CF.sub.3, CH.sub.2 F                                                                           CF.sub.3 (CHF).sub.2                                   65      CF.sub.3, CH.sub.2 F                                                                           CF.sub.3 CHFCF.sub.2                                   66      CF.sub.3, CH.sub.2 F                                                                           CF.sub.3 CHFCH.sub.2                                   67      CF.sub.3, CH.sub.2 F                                                                           CF.sub.3 CH.sub.2                                      68      CF.sub.3, CH.sub.2 F                                                                           CF.sub.3 (CH.sub.2).sub.2                              69      CF.sub.3, CH.sub.2 F                                                                           CF.sub.3 CH.sub.2 CF.sub.2                             70      CF.sub.3, CH.sub.2 F                                                                           CF.sub.3 CH.sub.2 CHF                                  71      CF.sub.3, CH.sub.2 F                                                                           CHF.sub.2 CF.sub.2                                     72      CF.sub.3, CH.sub.2 F                                                                           CHF.sub.2 (CF.sub.2).sub.2                             73      CF.sub.3, CH.sub.2 F                                                                           CHF.sub.2 CF.sub.2 CHF                                 74      CF.sub.3, CH.sub.2 F                                                                           CHF.sub.2 CF.sub.2 CH.sub.2                            75      CF.sub.3, CH.sub.2 F                                                                           CHF.sub.2 CHF                                          76      CF.sub.3, CH.sub.2 F                                                                           CHF.sub.2 (CHF).sub.2                                  77      CF.sub.3, CH.sub.2 F                                                                           CHF.sub.2 CHFCF.sub.2                                  78      CF.sub.3, CH.sub.2 F                                                                           CHF.sub.2 CHFCH.sub.2                                  79      CF.sub.3, CH.sub.2 F                                                                           CHF.sub.2 CH.sub.2                                     80      CF.sub.3, CH.sub.2 F                                                                           CHF.sub.2 (CH.sub.2).sub.2                             81      CF.sub.3, CH.sub.2 F                                                                           CHF.sub.2 CH.sub.2 CF.sub.2                            82      CF.sub.3, CH.sub.2 F                                                                           CHF.sub.2 CH.sub.2 CHF                                 83      CF.sub.3, CH.sub.2 F                                                                           CHF.sub.2 FCF.sub.2                                    84      CF.sub.3, CH.sub.2 F                                                                           CH.sub.2 F(CF.sub.2).sub.2                             85      CF.sub.3, CH.sub.2 F                                                                           CH.sub.2 FCF.sub.2 CHF                                 86      CF.sub.3, CH.sub.2 F                                                                           CH.sub.2 FCF.sub.2 CH.sub.2                            87      CF.sub.3, CH.sub.2 F                                                                           CH.sub.2 FCHF                                          88      CF.sub.3, CH.sub.2 F                                                                           CH.sub.2 (CHF).sub.2                                   89      CF.sub.3, CH.sub.2 F                                                                           CH.sub.2 FCHFCF.sub.2                                  90      CF.sub.3, CH.sub.2 F                                                                           CH.sub.2 FCHFCH.sub.2                                  91      CF.sub.3, CH.sub.2 F                                                                           CH.sub.2 FCH.sub.2                                     92      CF.sub.3, CH.sub.2 F                                                                           CH.sub.2 F(CH.sub.2).sub.2                             93      CF.sub.3, CH.sub.2 F                                                                           CH.sub.2 FCH.sub.2 CF.sub.2                            94      CF.sub.3, CH.sub.2 F                                                                           CH.sub.2 FCH.sub.2 CHF                                 95      CF.sub.3, CH.sub.2 F                                                                           CH.sub.3 CF.sub.2                                      96      CF.sub.3, CH.sub.2 F                                                                           CH.sub.3 (CF.sub.2).sub.2                              97      CF.sub.3, CH.sub.2 F                                                                           CH.sub.3 CF.sub.2 CHF                                  98      CF.sub.3, CH.sub.2 F                                                                           CH.sub.3 CF.sub.2 CH.sub.2                             99      CF.sub.3, CH.sub.2 F                                                                           CH.sub.3 CHF                                          100      CF.sub.3, CH.sub.2 F                                                                           CH.sub.3 (CHF).sub.2                                  101      CF.sub.3, CH.sub.2 F                                                                           CH.sub.3 CHFCF.sub.2                                  102      CF.sub.3, CH.sub.2 F                                                                           CH.sub.3 CHFCH.sub.2                                  103      CF.sub.3, CH.sub.2 F                                                                           CH.sub.3 CH.sub.2 CF.sub.2                            104      CF.sub.3, CH.sub.2 F                                                                           CH.sub.3 CH.sub.2 (CF.sub.2).sub.2                    105      CF.sub.3, CH.sub.2 F                                                                           CH.sub.3 (CH.sub.2).sub.2 CF.sub.2                    106      CF.sub.3, CH.sub.2 F                                                                           CH.sub.3 (CH.sub.2).sub.2 (CF.sub.2).sub.2            107      CF.sub.3, CH.sub.2 F                                                                           CH.sub.3 (CH.sub.2).sub.3 CF.sub.2                    108      CF.sub.3, CH.sub.2 F                                                                           CH.sub.3 (CH.sub.2).sub.3 (CF.sub.2).sub.2            109      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CF.sub.3                                              110      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CHF.sub.2                                             111      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CH.sub.2 F                                            112      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CH.sub.3                                              113      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CF.sub.3 CF.sub.2                                     114      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CF.sub.3 (CF.sub.2).sub.2                             115      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CF.sub.3 CF.sub.2 CHF                                 116      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CF.sub.3 CF.sub.2 CH.sub.2                            117      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CF.sub.3 CHF                                          118      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CF.sub.3 (CHF).sub.2                                  119      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CF.sub.3 CHFCF.sub.2                                  120      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CF.sub.3 CHFCH.sub.2                                  121      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CF.sub.3 CH.sub.2                                     122      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CF.sub.3 (CH.sub.2).sub.2                             123      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CF.sub.3 CH.sub.2 CF.sub.2                            124      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CF.sub.3 CH.sub.2 CHF                                 125      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CHF.sub.2 CF.sub.2                                    126      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CHF.sub.2 (CF.sub.2).sub.2                            127      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CHF.sub.2 CF.sub.2 CHF                                128      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CHF.sub.2 CF.sub.2 CH.sub.2                           129      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CHF.sub.2 CHF                                         130      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CHF.sub.2 (CHF).sub.2                                 131      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CHF.sub.2 CHFCF.sub.2                                 132      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CHF.sub.2 CHFCH.sub.2                                 133      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CHF.sub.2 CH.sub.2                                    134      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CHF.sub.2 (CH.sub.2).sub.2                            135      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CHF.sub.2 CH.sub.2 CF.sub.2                           136      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CHF.sub.2 CH.sub.2 CHF                                137      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CHF.sub.2 FCF.sub.2                                   138      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CH.sub.2 F(CF.sub.2).sub.2                            139      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CH.sub.2 FCF.sub.2 CHF                                140      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CH.sub.2 FCF.sub.2 CH.sub.2                           141      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CH.sub.2 FCHF                                         142      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CH.sub.2 F(CHF).sub.2                                 143      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CH.sub.2 FCHFCF.sub.2                                 144      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CH.sub.2 FCHFCH.sub.2                                 145      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CH.sub.2 FCH.sub.2                                    146      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CH.sub.2 F(CH.sub.2).sub.2                            147      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CH.sub.2 FCH.sub.2 CF.sub.2                           148      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CH.sub.2 FCH.sub.2 CHF                                149      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CH.sub.3 CF.sub.2                                     150      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CH.sub.3 (CF.sub.2).sub.2                             151      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CH.sub.3 CF.sub.2 CHF                                 152      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CH.sub.3 CF.sub.2 CH.sub.2                            153      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CH.sub.3 CHF                                          154      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CH.sub.3 (CHF).sub.2                                  155      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CH.sub.3 CHFCF.sub.2                                  156      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CH.sub.3 CHFCH.sub.2                                  157      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CH.sub.3 CH.sub.2 CF.sub.2                            158      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CH.sub.3 CH.sub.2 (CF.sub.2).sub. 2                   159      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CH.sub.3 (CH.sub.2).sub.2 CF.sub.2                    160      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CH.sub.3 (CH.sub.2).sub.2 (CF.sub.2).sub.2            161      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CH.sub.3 (CH.sub.2).sub.3 CF.sub.2                    162      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CH.sub.3 (CH.sub.2).sub.3 (CF.sub.2).sub.2            163      CHF.sub.2, CH.sub.2 F                                                                          CF.sub.3                                              164      CHF.sub.2, CH.sub.2 F                                                                          CHF.sub.2                                             165      CHF.sub.2, CH.sub.2 F                                                                          CH.sub.2 F                                            166      CHF.sub.2, CH.sub.2 F                                                                          CH.sub.3                                              167      CHF.sub.2, CH.sub.2 F                                                                          CF.sub.3 CF.sub.2                                     168      CHF.sub.2, CH.sub.2 F                                                                          CF.sub.3 (CF.sub.2).sub.2                             169      CHF.sub.2, CH.sub.2 F                                                                          CF.sub.3 CF.sub.2 CHF                                 170      CHF.sub.2, CH.sub.2 F                                                                          CF.sub.3 CF.sub.2 CH.sub.2                            171      CHF.sub.2, CH.sub.2 F                                                                          CF.sub.3 CHF                                          172      CHF.sub.2, CH.sub.2 F                                                                          CF.sub.3 (CHF).sub.2                                  173      CHF.sub.2, CH.sub.2 F                                                                          CF.sub. 3 CHFCF.sub.2                                 174      CHF.sub.2, CH.sub.2 F                                                                          CF.sub.3 CHFCH.sub.2                                  175      CHF.sub.2, CH.sub.2 F                                                                          CF.sub.3 CH.sub.2                                     176      CHF.sub.2, CH.sub.2 F                                                                          CF.sub.3 (CH.sub.2).sub.2                             177      CHF.sub.2, CH.sub.2 F                                                                          CF.sub.3 CH.sub.2 CF.sub.2                            178      CHF.sub.2, CH.sub.2 F                                                                          CF.sub.3 CH.sub.2 CHF                                 179      CHF.sub.2, CH.sub.2 F                                                                          CHF.sub.2 CF.sub.2                                    180      CHF.sub.2, CH.sub.2 F                                                                          CHF.sub.2 (CF.sub.2).sub.2                            181      CHF.sub.2, CH.sub.2 F                                                                          CHF.sub.2 CF.sub.2 CHF                                182      CHF.sub.2, CH.sub.2 F                                                                          CHF.sub.2 CF.sub.2 CH.sub.2                           183      CHF.sub.2, CH.sub.2 F                                                                          CHF.sub.2 CHF                                         184      CHF.sub.2, CH.sub.2 F                                                                          CHF.sub.2 (CHF).sub.2                                 185      CHF.sub.2, CH.sub.2 F                                                                          CHF.sub.2 CHFCF.sub.2                                 186      CHF.sub.2, CH.sub.2 F                                                                          CHF.sub.2 CHFCH.sub.2                                 187      CHF.sub.2, CH.sub.2 F                                                                          CHF.sub.2 CH.sub.2                                    188      CHF.sub.2, CH.sub.2 F                                                                          CHF.sub.2 (CH.sub.2).sub.2                            189      CHF.sub.2, CH.sub.2 F                                                                          CHF.sub. 2 CH.sub.2 CF.sub.2                          190      CHF.sub.2, CH.sub.2 F                                                                          CHF.sub.2 CH.sub.2 CHF                                191      CHF.sub.2, CH.sub.2 F                                                                          CHF.sub.2 FCF.sub.2                                   192      CHF.sub.2, CH.sub.2 F                                                                          CH.sub.2 F(CF.sub.2).sub.2                            193      CHF.sub.2, CH.sub.2 F                                                                          CH.sub.2 FCF.sub.2 CHF                                194      CHF.sub.2, CH.sub.2 F                                                                          CH.sub.2 FCF.sub.2 CH.sub.2                           195      CHF.sub.2, CH.sub.2 F                                                                          CH.sub.2 FCHF                                         196      CHF.sub.2, CH.sub.2 F                                                                          CH.sub.2 F(CHF).sub.2                                 197      CHF.sub.2, CH.sub.2 F                                                                          CH.sub.2 FCHFCF.sub.2                                 198      CHF.sub.2, CH.sub.2 F                                                                          CH.sub.2 FCHFCH.sub.2                                 199      CHF.sub.2, CH.sub.2 F                                                                          CH.sub.2 FCH.sub.2                                    200      CHF.sub.2, CH.sub.2 F                                                                          CH.sub.2 F(CH.sub.2).sub.2                            201      CHF.sub.2, CH.sub.2 F                                                                          CH.sub.2 FCH.sub.2 CF.sub.2                           202      CHF.sub.2, CH.sub.2 F                                                                          CH.sub.2 FCH.sub.2 CHF                                203      CHF.sub.2, CH.sub.2 F                                                                          CH.sub.3 CF.sub.2                                     204      CHF.sub.2, CH.sub.2 F                                                                          CH.sub.3 (CF.sub.2).sub.2                             205      CHF.sub.2, CH.sub.2 F                                                                          CH.sub.3 CF.sub.2 CHF                                 206      CHF.sub.2, CH.sub.2 F                                                                          CH.sub.3 CF.sub.2 CH.sub.2                            207      CHF.sub.2, CH.sub.2 F                                                                          CH.sub.3 CHF                                          208      CHF.sub.2, CH.sub.2 F                                                                          CH.sub.3 (CHF).sub.2                                  209      CHF.sub.2, CH.sub.2 F                                                                          CH.sub.3 CHFCF.sub.2                                  210      CHF.sub.2, CH.sub.2 F                                                                          CH.sub.3 CHFCH.sub.2                                  211      CHF.sub.2, CH.sub.2 F                                                                          CH.sub.3 CH.sub.2 CF.sub.2                            212      CHF.sub.2, CH.sub.2 F                                                                          CH.sub.3 CH.sub.2 (CF.sub.2).sub.2                    213      CHF.sub.2, CH.sub.2 F                                                                          CH.sub.3 (CH.sub.2).sub.2 CF.sub.2                    214      CHF.sub.2, CH.sub.2 F                                                                          CH.sub.3 (CH.sub.2).sub.2 (CF.sub.2).sub.2            215      CHF.sub.2, CH.sub.2 F                                                                          CH.sub.3 (CH.sub.2).sub.3 CF.sub.2                    216      CHF.sub.2, CH.sub.2 F                                                                          CH.sub.3 (CH.sub.2).sub.3 (CF.sub.2).sub.2            217      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CF.sub.3                                              218      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CHF.sub.2                                             219      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CH.sub.2 F                                            220      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CH.sub.3                                              221      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CF.sub.3 CF.sub.2                                     222      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CF.sub.3 (CF.sub.2).sub.2                             223      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CF.sub.3 CF.sub.2 CHF                                 224      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CF.sub.3 CF.sub.2 CH.sub.2                            225      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CF.sub.3 CHF                                          226      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CF.sub.3 (CHF).sub.2                                  227      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CF.sub.3 CHFCF.sub.2                                  228      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CF.sub.3 CHFCH.sub.2                                  229      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CF.sub.3 CH.sub.2                                     230      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CF.sub.3 (CH.sub.2).sub.2                             231      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CF.sub.3 CH.sub.2 CF.sub.2                            232      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CF.sub.3 CH.sub.2 CHF                                 233      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CHF.sub.2 CF.sub.2                                    234      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CHF.sub.2 (CF.sub.2).sub.2                            235      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CHF.sub.2 CF.sub.2 CHF                                236      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CHF.sub.2 CF.sub.2 CH.sub.2                           237      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CHF.sub.2 CHF                                         238      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CHF.sub.2 (CHF).sub.2                                 239      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CHF.sub.2 CHFCF.sub.2                                 240      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CHF.sub.2 CHFCH.sub.2                                 241      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CHF.sub.2 CH.sub.2                                    242      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CHF.sub.2 (CH.sub.2).sub.2                            243      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CHF.sub.2 CH.sub.2 CF.sub.2                           244      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CHF.sub.2 CH.sub.2 CHF                                245      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CHF.sub.2 FCF.sub.2                                   246      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CH.sub.2 F(CF.sub.2).sub.2                            247      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CH.sub. 2 FCF.sub.2 CHF                               248      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CH.sub.2 FCF.sub.2 CH.sub.2                           249      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CH.sub.2 FCHF                                         250      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CHF.sub.2 (CHF).sub.2                                 251      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CH.sub.2 FCHFCF.sub.2                                 252      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CH.sub.2 FCHFCH.sub.2                                 253      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CH.sub.2 FCH.sub.2                                    254      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CH.sub.2 F(CH.sub.2).sub.2                            255      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CH.sub.2 FCH.sub.2 CF.sub.2                           256      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CH.sub.2 FCH.sub.2 CHF                                257      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CH.sub.3 CF.sub.2                                     258      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CH.sub.3 (CF.sub.2).sub.2                             259      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CH.sub.3 CF.sub.2 CHF                                 260      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CH.sub.3 CF.sub.2 CH.sub.2                            261      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CH.sub.3 CHF                                          262      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CH.sub.3 (CHF).sub.2                                  263      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CH.sub.3 CHFCF.sub.2                                  264      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CH.sub.3 CHFCH.sub.2                                  265      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CH.sub.3 CH.sub.2 CF.sub.2                            266      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CH.sub.3 CH.sub.2 (CF.sub.2).sub.2                    267      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CH.sub.3 (CH.sub.2).sub.2 CF.sub.2                    268      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CH.sub.3 (CH.sub.2).sub.2 (CF.sub.2).sub.2            269      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CH.sub.3 (CH.sub.2).sub.3 CF.sub.2                    270      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CH.sub.3 (CH.sub.2).sub.3 (CF.sub.2).sub.2            271      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CF.sub.3                                              272      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CHF.sub.2                                             273      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CH.sub.2 F                                            274      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CH.sub.3                                              275      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CF.sub.3 CF.sub.2                                     276      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CF.sub.3 (CF.sub.2).sub.2                             277      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CF.sub.3 CF.sub.2 CHF                                 278      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CF.sub.3 CF.sub.2 CH.sub.2                            279      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CF.sub.3 CHF                                          280      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CF.sub.3 (CHF).sub.2                                  281      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CF.sub.3 CHFCF.sub.2                                  282      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CF.sub.3 CHFCH.sub.2                                  283      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CF.sub.3 CH.sub.2                                     284      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CF.sub.3 (CH.sub.2).sub.2                             285      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CF.sub.3 CH.sub.2 CF.sub.2                            286      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CF.sub.3 CH.sub.2 CHF                                 287      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CHF.sub.2 CF.sub.2                                    288      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CHF.sub.2 (CF.sub.2).sub.2                            289      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CHF.sub.2 CF.sub.2 CHF                                290      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CHF.sub.2 CF.sub.2 CH.sub.2                           291      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CHF.sub.2 CHF                                         292      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CHF.sub.2 (CHF).sub.2                                 293      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CHF.sub.2 CHFCF.sub.2                                 294      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CHF.sub.2 CHFCH.sub.2                                 295      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CHF.sub.2 CH.sub.2                                    296      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CHF.sub.2 (CH.sub.2).sub.2                            297      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CHF.sub.2 CH.sub.2 CF.sub.2                           298      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CHF.sub.2 CH.sub.2 CHF                                299      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CHF.sub.2 FCF.sub.2                                   300      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CH.sub.2 F(CF.sub.2).sub.2                            301      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CH.sub.2 FCF.sub.2 CHF                                302      CH.sub. 2 F, CH.sub.3 CF.sub.2                                                                 CH.sub.2 FCF.sub.2 CH.sub.2                           303      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CH.sub.2 FCHF                                         304      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CHF.sub.2 (CHF).sub.2                                 305      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CH.sub.2 FCHFCF.sub.2                                 306      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CH.sub.2 FCHFCH.sub.2                                 307      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CH.sub.2 FCH.sub.2                                    308      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CH.sub.2 F(CH.sub.2).sub.2                            309      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CH.sub.2 FCH.sub.2 CF.sub.2                           310      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CH.sub.2 FCH.sub.2 CHF                                311      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CH.sub.3 CF.sub.2                                     312      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CH.sub.3 (CF.sub.2).sub.2                             313      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CH.sub.3 CF.sub.2 CHF                                 314      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CH.sub.3 CF.sub.2 CH.sub.2                            315      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CH.sub.3 CHF                                          316      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CH.sub.3 (CHF).sub.2                                  317      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CH.sub.3 CHFCF.sub.2                                  318      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CH.sub.3 CHFCH.sub.2                                  319      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CH.sub.3 CH.sub.2 CF.sub.2                            320      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CH.sub.3 CH.sub.2 (CF.sub.2).sub.2                    321      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CH.sub.3 (CH.sub.2).sub.2 CF.sub.2                    322      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CH.sub.3 (CH.sub.2).sub.2 (CF.sub.2).sub.2            323      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CH.sub.3 (CH.sub.2).sub.3 CF.sub.2                    324      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CH.sub.3 (CH.sub.2).sub.3 (CF.sub.2).sub.2            325      CF.sub.3, CF.sub.3                                                                             CF.sub.3                                              326      CF.sub.3, CF.sub.3                                                                             CHF.sub.2                                             327      CF.sub.3, CF.sub.3                                                                             CH.sub.2 F                                            328      CF.sub.3, CF.sub.3                                                                             CH.sub.3                                              329      CF.sub.3, CF.sub.3                                                                             CF.sub. 3 CF.sub.2                                    330      CF.sub.3, CF.sub.3                                                                             CF.sub.3 (CF.sub.2).sub.2                             331      CF.sub.3, CF.sub.3                                                                             CF.sub.3 CF.sub.2 CHF                                 332      CF.sub.3, CF.sub.3                                                                             CF.sub.3 CF.sub.2 CH.sub.2                            333      CF.sub.3, CF.sub.3                                                                             CF.sub.3 CHF                                          334      CF.sub.3, CF.sub.3                                                                             CF.sub.3 (CHF).sub.2                                  335      CF.sub.3, CF.sub.3                                                                             CF.sub.3 CHFCF.sub.2                                  336      CF.sub.3, CF.sub.3                                                                             CF.sub.3 CHFCH.sub.2                                  337      CF.sub.3, CF.sub.3                                                                             CF.sub.3 CH.sub.2                                     338      CF.sub.3, CF.sub.3                                                                             CF.sub.3 (CH.sub.2).sub.2                             339      CF.sub.3, CF.sub.3                                                                             CF.sub.3 CH.sub.2 CF.sub.2                            340      CF.sub.3, CF.sub.3                                                                             CF.sub.3 CH.sub.2 CHF                                 341      CF.sub.3, CF.sub.3                                                                             CHF.sub.2 CF.sub.2                                    342      CF.sub.3, CF.sub.3                                                                             CHF.sub.2 (CF.sub.2).sub.2                            343      CF.sub.3, CF.sub.3                                                                             CHF.sub.2 CF.sub.2 CHF                                344      CF.sub.3, CF.sub.3                                                                             CHF.sub.2 CF.sub.2 CH.sub.2                           345      CF.sub.3, CF.sub.3                                                                             CHF.sub.2 CHF                                         346      CF.sub.3, CF.sub.3                                                                             CHF.sub.2 (CHF).sub.2                                 347      CF.sub.3, CF.sub.3                                                                             CHF.sub.2 CHFCF.sub.2                                 348      CF.sub.3, CF.sub.3                                                                             CHF.sub.2 CHFCH.sub.2                                 349      CF.sub.3, CF.sub.3                                                                             CHF.sub.2 CH.sub.2                                    350      CF.sub.3, CF.sub.3                                                                             CHF.sub.2 (CH.sub.2).sub.2                            351      CF.sub.3, CF.sub.3                                                                             CHF.sub.2 CH.sub.2 CF.sub.2                           352      CF.sub.3, CF.sub.3                                                                             CHF.sub.2 CH.sub.2 CHF                                353      CF.sub.3, CF.sub.3                                                                             CHF.sub.2 FCF.sub.2                                   354      CF.sub.3, CF.sub.3                                                                             CH.sub.2 F(CF.sub.2).sub.2                            355      CF.sub.3, CF.sub.3                                                                             CH.sub.2 FCF.sub.2 CHF                                356      CF.sub.3, CF.sub.3                                                                             CH.sub.2 FCF.sub.2 CH.sub.2                           357      CF.sub.3, CF.sub.3                                                                             CH.sub.2 FCHF                                         358      CF.sub.3, CF.sub.3                                                                             CHF.sub.2 (CHF).sub.2                                 359      CF.sub.3, CF.sub.3                                                                             CH.sub.2 FCHFCF.sub.2                                 360      CF.sub.3, CF.sub.3                                                                             CH.sub.2 FCHFCH.sub.2                                 361      CF.sub.3, CF.sub.3                                                                             CH.sub.2 FCH.sub. 2                                   362      CF.sub.3, CF.sub.3                                                                             CH.sub.2 F(CH.sub.2).sub.2                            363      CF.sub.3, CF.sub.3                                                                             CH.sub.2 FCH.sub.2 CF.sub.2                           364      CF.sub.3, CF.sub.3                                                                             CH.sub.2 FCH.sub.2 CHF                                365      CF.sub.3, CF.sub.3                                                                             CH.sub.3 CF.sub.2                                     366      CF.sub.3, CF.sub.3                                                                             CH.sub.3 (CF.sub.2).sub.2                             367      CF.sub.3, CF.sub.3                                                                             CH.sub.3 CF.sub.2 CHF                                 368      CF.sub.3, CF.sub.3                                                                             CH.sub.3 CF.sub.2 CH.sub.2                            369      CF.sub.3, CF.sub.3                                                                             CH.sub.3 CHF                                          370      CF.sub.3, CF.sub.3                                                                             CH.sub.3 (CHF).sub.2                                  371      CF.sub.3, CF.sub.3                                                                             CH.sub.3 CHFCF.sub.2                                  372      CF.sub.3, CF.sub.3                                                                             CH.sub.3 CHFCH.sub.2                                  373      CF.sub.3, CF.sub.3                                                                             CH.sub.3 CH.sub.2 CF.sub.2                            374      CF.sub.3, CF.sub.3                                                                             CH.sub.3 CH.sub.2 (CF.sub.2).sub.2                    375      CF.sub.3, CF.sub.3                                                                             CH.sub.3 (CH.sub.2).sub.2 CF.sub.2                    376      CF.sub.3, CF.sub.3                                                                             CH.sub.3 (CH.sub.2).sub.2 (CF.sub. 2).sub.2           377      CF.sub.3, CF.sub.3                                                                             CH.sub.3 (CH.sub.2).sub.3 CF.sub.2                    378      CF.sub.3, CF.sub.3                                                                             CH.sub.3 (CH.sub.2).sub.3 (CF.sub.2).sub.2            379      CHF.sub.2, CHF.sub.2                                                                           CF.sub.3                                              380      CHF.sub.2, CHF.sub.2                                                                           CHF.sub.2                                             381      CHF.sub.2, CHF.sub.2                                                                           CH.sub.2 F                                            382      CHF.sub.2, CHF.sub.2                                                                           CH.sub.3                                              383      CHF.sub.2, CHF.sub.2                                                                           CF.sub.3 CF.sub.2                                     384      CHF.sub.2, CHF.sub.2                                                                           CF.sub.3 (CF.sub.2).sub.2                             385      CHF.sub.2, CHF.sub.2                                                                           CF.sub.3 CF.sub.2 CHF                                 386      CHF.sub.2, CHF.sub.2                                                                           CF.sub.3 CF.sub.2 CH.sub.2                            387      CHF.sub.2, CHF.sub.2                                                                           CF.sub.3 CHF                                          388      CHF.sub.2, CHF.sub.2                                                                           CF.sub.3 (CHF).sub.2                                  389      CHF.sub.2, CHF.sub.2                                                                           CF.sub.3 CHFCF.sub.2                                  390      CHF.sub.2, CHF.sub.2                                                                           CF.sub.3 CHFCH.sub.2                                  391      CHF.sub.2, CHF.sub.2                                                                           CF.sub.3 CH.sub.2                                     392      CHF.sub.2, CHF.sub.2                                                                           CF.sub.3 (CH.sub.2).sub. 2                            393      CHF.sub.2, CHF.sub.2                                                                           CF.sub.3 CH.sub.2 CF.sub.2                            394      CHF.sub.2, CHF.sub.2                                                                           CF.sub.3 CH.sub.2 CHF                                 395      CHF.sub.2, CHF.sub.2                                                                           CHF.sub.2 CF.sub.2                                    396      CHF.sub.2, CHF.sub.2                                                                           CHF.sub.2 (CF.sub.2).sub.2                            397      CHF.sub.2, CHF.sub.2                                                                           CHF.sub.2 CF.sub.2 CHF                                398      CHF.sub.2, CHF.sub.2                                                                           CHF.sub.2 CF.sub.2 CH.sub.2                           399      CHF.sub.2, CHF.sub.2                                                                           CHF.sub.2 CHF                                         400      CHF.sub.2, CHF.sub.2                                                                           CHF.sub.2 (CHF).sub.2                                 401      CHF.sub.2, CHF.sub.2                                                                           CHF.sub.2 CHFCF.sub.2                                 402      CHF.sub.2, CHF.sub.2                                                                           CHF.sub.2 CHFCH.sub.2                                 403      CHF.sub.2, CHF.sub.2                                                                           CHF.sub.2 CH.sub.2                                    404      CHF.sub.2, CHF.sub.2                                                                           CHF.sub.2 (CH.sub.2).sub.2                            405      CHF.sub.2, CHF.sub.2                                                                           CHF.sub.2 CH.sub.2 CF.sub.2                           406      CHF.sub.2, CHF.sub.2                                                                           CHF.sub.2 CH.sub.2 CHF                                407      CHF.sub.2, CHF.sub.2                                                                           CHF.sub.2 FCF.sub.2                                   408      CHF.sub.2, CHF.sub.2                                                                           CH.sub.2 F(CF.sub. 2).sub.2                           409      CHF.sub.2, CHF.sub.2                                                                           CH.sub.2 FCF.sub.2 CHF                                410      CHF.sub.2, CHF.sub.2                                                                           CH.sub.2 FCF.sub.2 CH.sub.2                           411      CHF.sub.2, CHF.sub.2                                                                           CH.sub.2 FCHF                                         412      CHF.sub.2, CHF.sub.2                                                                           CHF.sub.2 (CHF).sub.2                                 413      CHF.sub.2, CHF.sub.2                                                                           CH.sub.2 FCHFCF.sub.2                                 414      CHF.sub.2, CHF.sub.2                                                                           CH.sub.2 FCHFCH.sub.2                                 415      CHF.sub.2, CHF.sub.2                                                                           CH.sub.2 FCH.sub.2                                    416      CHF.sub.2, CHF.sub.2                                                                           CH.sub.2 F(CH.sub.2).sub.2                            417      CHF.sub.2, CHF.sub.2                                                                           CH.sub.2 FCH.sub.2 CF.sub.2                           418      CHF.sub.2, CHF.sub.2                                                                           CH.sub.2 FCH.sub.2 CHF                                419      CHF.sub.2, CHF.sub.2                                                                           CH.sub.3 CF.sub.2                                     420      CHF.sub.2, CHF.sub.2                                                                           CH.sub.3 (CF.sub.2).sub.2                             421      CHF.sub.2, CHF.sub.2                                                                           CH.sub.3 CF.sub.2 CHF                                 422      CHF.sub.2, CHF.sub.2                                                                           CH.sub.3 CF.sub.2 CH.sub.2                            423      CHF.sub.2, CHF.sub.2                                                                           CH.sub.3 CHF                                          424      CHF.sub.2, CHF.sub.2                                                                           CH.sub.3 (CHF).sub. 2                                 425      CHF.sub.2, CHF.sub.2                                                                           CH.sub.3 CHFCF.sub.2                                  426      CHF.sub.2, CHF.sub.2                                                                           CH.sub.3 CHFCH.sub.2                                  427      CHF.sub.2, CHF.sub.2                                                                           CH.sub.3 CH.sub.2 CF.sub.2                            428      CHF.sub.2, CHF.sub.2                                                                           CH.sub.3 CH.sub.2 (CF.sub.2).sub.2                    429      CHF.sub.2, CHF.sub.2                                                                           CH.sub.3 (CH.sub.2).sub.2 CF.sub.2                    430      CHF.sub.2, CHF.sub.2                                                                           CH.sub.3 (CH.sub.2).sub.2 (CF.sub.2).sub.2            431      CHF.sub.2, CHF.sub.2                                                                           CH.sub.3 (CH.sub.2).sub.3 CF.sub.2                    432      CHF.sub.2, CHF.sub.2                                                                           CH.sub.3 (CH.sub.2).sub.3 (CF.sub.2).sub.2            433      CH.sub.2, CHF.sub.2 F                                                                          CF.sub.3                                              434      CH.sub.2, CHF.sub.2 F                                                                          CHF.sub.2                                             435      CH.sub.2, CHF.sub.2 F                                                                          CH.sub.2 F                                            436      CH.sub.2, CHF.sub.2 F                                                                          CH.sub.3                                              437      CH.sub.2, CHF.sub.2 F                                                                          CF.sub.3 CF.sub.2                                     438      CH.sub.2, CHF.sub.2 F                                                                          CF.sub.3 (CF.sub.2).sub.2                             439      CH.sub.2, CHF.sub.2 F                                                                          CF.sub.3 CF.sub. 2 CHF                                440      CH.sub.2, CHF.sub.2 F                                                                          CF.sub.3 CF.sub.2 CH.sub.2                            441      CH.sub.2, CHF.sub.2 F                                                                          CF.sub.3 CHF                                          442      CH.sub.2, CHF.sub.2 F                                                                          CF.sub.3 (CHF).sub.2                                  443      CH.sub.2, CHF.sub.2 F                                                                          CF.sub.3 CHFCF.sub.2                                  444      CH.sub.2, CHF.sub.2 F                                                                          CF.sub.3 CHFCH.sub.2                                  445      CH.sub.2, CHF.sub.2 F                                                                          CF.sub.3 CH.sub.2                                     446      CH.sub.2, CHF.sub.2 F                                                                          CF.sub.3 (CH.sub.2).sub.2                             447      CH.sub.2, CHF.sub.2 F                                                                          CF.sub.3 CH.sub.2 CF.sub.2                            448      CH.sub.2, CHF.sub.2 F                                                                          CF.sub.3 CH.sub.2 CHF                                 449      CH.sub.2, CHF.sub.2 F                                                                          CHF.sub.2 CF.sub.2                                    450      CH.sub.2, CHF.sub.2 F                                                                          CHF.sub.2 (CF.sub.2).sub.2                            451      CH.sub.2, CHF.sub.2 F                                                                          CHF.sub.2 CF.sub.2 CHF                                452      CH.sub.2, CHF.sub.2 F                                                                          CHF.sub.2 CF.sub.2 CH.sub.2                           453      CH.sub.2, CHF.sub.2 F                                                                          CHF.sub.2 CHF                                         454      CH.sub.2, CHF.sub.2 F                                                                          CHF.sub.2 (CHF).sub.2                                 455      CH.sub.2, CHF.sub.2 F                                                                          CHF.sub.2 CHFCF.sub.2                                 456      CH.sub.2, CHF.sub.2 F                                                                          CHF.sub.2 CHFCH.sub.2                                 457      CH.sub.2, CHF.sub.2 F                                                                          CHF.sub.2 CH.sub.2                                    458      CH.sub.2, CHF.sub.2 F                                                                          CHF.sub.2 (CH.sub.2).sub.2                            459      CH.sub.2, CHF.sub.2 F                                                                          CHF.sub.2 CH.sub.2 CF.sub.2                           460      CH.sub.2, CHF.sub.2 F                                                                          CHF.sub.2 CH.sub.2 CHF                                461      CH.sub.2, CHF.sub.2 F                                                                          CHF.sub.2 FCF.sub.2                                   462      CH.sub.2, CHF.sub.2 F                                                                          CH.sub.2 F(CF.sub.2).sub.2                            463      CH.sub.2, CHF.sub.2 F                                                                          CH.sub.2 FCF.sub.2 CHF                                464      CH.sub.2, CHF.sub.2 F                                                                          CH.sub.2 FCF.sub.2 CH.sub.2                           465      CH.sub.2, CHF.sub.2 F                                                                          CH.sub.2 FCHF                                         466      CH.sub.2, CHF.sub.2 F                                                                          CHF.sub.2 (CHF).sub.2                                 467      CH.sub.2, CHF.sub.2 F                                                                          CH.sub.2 FCHFCF.sub.2                                 468      CH.sub.2, CHF.sub.2 F                                                                          CH.sub.2 FCHFCH.sub.2                                 469      CH.sub.2, CHF.sub.2 F                                                                          CH.sub.2 FCH.sub.2                                    470      CH.sub.2, CHF.sub.2 F                                                                          CH.sub.2 F(CH.sub.2).sub.2                            471      CH.sub.2, CHF.sub.2 F                                                                          CH.sub.2 FCH.sub.2 CF.sub. 2                          472      CH.sub.2, CHF.sub.2 F                                                                          CH.sub.2 FCH.sub.2 CHF                                473      CH.sub.2, CHF.sub.2 F                                                                          CH.sub.3 CF.sub.2                                     474      CH.sub.2, CHF.sub.2 F                                                                          CH.sub.3 (CF.sub.2).sub.2                             475      CH.sub.2, CHF.sub.2 F                                                                          CH.sub.3 CF.sub.2 CHF                                 476      CH.sub.2, CHF.sub.2 F                                                                          CH.sub.3 CF.sub.2 CH.sub.2                            477      CH.sub.2, CHF.sub.2 F                                                                          CH.sub.3 CHF                                          478      CH.sub.2, CHF.sub.2 F                                                                          CH.sub.3 (CHF).sub.2                                  479      CH.sub.2, CHF.sub.2 F                                                                          CH.sub.3 CHFCF.sub.2                                  480      CH.sub.2, CHF.sub.2 F                                                                          CH.sub.3 CHFCH.sub.2                                  481      CH.sub.2, CHF.sub.2 F                                                                          CH.sub.3 CH.sub.2 CF.sub.2                            482      CH.sub.2, CHF.sub.2 F                                                                          CH.sub.3 CH.sub.2 (CF.sub.2).sub.2                    483      CH.sub.2, CHF.sub.2 F                                                                          CH.sub.3 (CH.sub.2).sub.2 CF.sub.2                    484      CH.sub.2, CHF.sub.2 F                                                                          CH.sub.3 (CH.sub.2).sub.2 (CF.sub.2).sub.2            485      CH.sub.2, CHF.sub.2 F                                                                          CH.sub.3 (CH.sub.2).sub.3 CF.sub.2                    486      CH.sub.2, CHF.sub.2 F                                                                          CH.sub. 3 (CH.sub.2).sub.3 (CF.sub.2).sub.2           487      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CF.sub.3                                              488      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CHF.sub.2                                             489      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CH.sub.2 F                                            490      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CH.sub.3                                              491      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CF.sub.3 CF.sub.2                                     492      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CF.sub.3 (CF.sub.2).sub.2                             493      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CF.sub.3 CF.sub.2 CHF                                 494      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CF.sub.3 CF.sub.2 CH.sub.2                            495      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CF.sub.3 CHF                                          496      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CF.sub.3 (CHF).sub.2                                  497      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CF.sub.3 CHFCF.sub.2                                  498      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CF.sub.3 CHFCH.sub.2                                  499      CH.sub.3 CF.sub. 2, CH.sub.3 CF.sub.2                                                          CF.sub.3 CH.sub.2                                     500      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CF.sub.3 (CH.sub.2).sub.2                             501      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CF.sub.3 CH.sub.2 CF.sub.2                            502      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CF.sub.3 CH.sub.2 CHF                                 503      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CHF.sub.2 CF.sub.2                                    504      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CHF.sub.2 (CF.sub.2).sub.2                            505      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CHF.sub.2 CF.sub.2 CHF                                506      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CHF.sub.2 CF.sub.2 CH.sub.2                           507      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CHF.sub.2 CHF                                         508      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CHF.sub.2 (CHF).sub.2                                 509      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CHF.sub.2 CHFCF.sub.2                                 510      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CHF.sub.2 CHFCH.sub.2                                 511      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CHF.sub.2 CH.sub.2                                    512      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CHF.sub.2 (CH.sub.2).sub.2                            513      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CHF.sub.2 CH.sub.2 CF.sub.2                           514      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CHF.sub.2 CH.sub.2 CHF                                515      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CHF.sub.2 FCF.sub.2                                   516      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CH.sub.2 F(CF.sub.2).sub.2                            517      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CH.sub.2 FCF.sub.2 CHF                                518      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CH.sub.2 FCF.sub.2 CH.sub.2                           519      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CH.sub.2 FCHF                                         520      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CHF.sub.2 (CHF).sub.2                                 521      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CH.sub.2 FCHFCF.sub.2                                 522      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CH.sub.2 FCHFCH.sub.2                                 523      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CH.sub.2 FCH.sub.2                                    524      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CH.sub.2 F(CH.sub.2).sub.2                            525      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CH.sub.2 FCH.sub.2 CF.sub.2                           526      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CH.sub.2 FCH.sub.2 CHF                                527      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CH.sub.3 CF.sub.2                                     528      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CH.sub.3 (CF.sub.2).sub.2                             529      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CH.sub.3 CF.sub.2 CHF                                 530      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CH.sub.3 CF.sub.2 CH.sub.2                            531      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CH.sub.3 CHF                                          532      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CH.sub.3 (CHF).sub.2                                  533      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CH.sub.3 CHFCF.sub.2                                  534      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CH.sub.3 CHFCH.sub.2                                  535      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CH.sub.3 CH.sub.2 CF.sub.2                            536      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CH.sub.3 CH.sub.2 (CF.sub.2).sub.2                    537      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CH.sub.3 (CH.sub.2).sub.2 CF.sub.2                    538      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CH.sub.3 (CH.sub.2).sub.2 (CF.sub.2).sub.2            539      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CH.sub.3 (CH.sub.2).sub.3 CF.sub.2                    540      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CH.sub.3 (CH.sub.2).sub.3 (CF.sub.2).sub.2            541      CF.sub.3, CF.sub.3                                                                             CF.sub.3                                              542      CF.sub.3, CF.sub.3                                                                             CF.sub.3 CF.sub.2                                     543      CF.sub.3, CF.sub.3                                                                             CF.sub.3 (CF.sub.2).sub.2                             544      CF.sub.3, CHF.sub.2                                                                            CH.sub.3 CH.sub.2                                     545      CF.sub.3, CHF.sub.2                                                                            CH.sub.3 (CH.sub.2).sub.2                             546      CF.sub.3, CHF.sub.2                                                                            CH.sub.3 (CH.sub.2).sub.3                             547      CF.sub.3, CH.sub.2 F                                                                           CH.sub.3 CH.sub.3                                     548      CF.sub.3, CH.sub.2 F                                                                           CH.sub.3 (CH.sub.2).sub.2                             549      CF.sub.3, CH.sub.2 F                                                                           CH.sub.3 (CH.sub.2).sub.3                             550      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CH.sub.3 CH.sub.2                                     551      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CH.sub.3 (CH.sub.2).sub.2                             552      CF.sub.3, CH.sub.3 CF.sub.2                                                                    CH.sub.3 (CH.sub.2).sub.3                             553      CHF.sub.2, CH.sub.2 F                                                                          CH.sub.3 CH.sub.2                                     554      CHF.sub.2, CH.sub.2 F                                                                          CH.sub.3 (CH.sub.2).sub.2                             555      CHF.sub.2, CH.sub.2 F                                                                          CH.sub.3 (CH.sub.2).sub.3                             556      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CH.sub.3 CH.sub.2                                     557      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CH.sub.3 (CH.sub.2).sub.2                             558      CHF.sub.2, CH.sub.3 CF.sub.2                                                                   CH.sub.3 (CH.sub.2).sub.3                             559      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CH.sub.3 CH.sub.2                                     560      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CH.sub.3 (CH.sub.2).sub.2                             561      CH.sub.2 F, CH.sub.3 CF.sub.2                                                                  CH.sub. 3 (CH.sub.2).sub.3                            562      CF.sub.3, CF.sub.3                                                                             CH.sub.3 CH.sub.2                                     563      CF.sub.3, CF.sub.3                                                                             CH.sub.3 (CH.sub.2).sub.2                             564      CF.sub.3, CF.sub.3                                                                             CH.sub.3 (CH.sub.2).sub.3                             565      CHF.sub.2, CHF.sub.2                                                                           CH.sub.3 CH.sub.2                                     566      CHF.sub.2, CHF.sub.2                                                                           CH.sub.3 (CH.sub.2).sub.2                             567      CHF.sub.2, CHF.sub.2                                                                           CH.sub.3 (CH.sub.2).sub.3                             568      CH.sub.2 F, CH.sub.2 F                                                                         CH.sub.3 CH.sub.2                                     569      CH.sub.2 F, CH.sub.2 F                                                                         CH.sub.3 (CH.sub.2).sub.2                             570      CH.sub.2 F, CH.sub.2 F                                                                         CH.sub.3 (CH.sub.2).sub.3                             571      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CH.sub.3 CH.sub.2                                     572      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CH.sub.3 (CH.sub.2).sub.2                             573      CH.sub.3 CF.sub.2, CH.sub.3 CF.sub.2                                                           CH.sub.3 (CH.sub.2).sub.3                             ______________________________________                                    

EXAMPLES 574-1,146

Metal coupons are soiled with various types of oil. The soiled metal coupons are immersed in the novel solvents of Table I above for a period of 15 seconds to 2 minutes, removed, and allowed to air dry. Upon visual inspection, the soil appears to be substantially removed.

EXAMPLES 1,147-1,719

Metal coupons are soiled with various types of oil. The soiled metal coupons are wiped with the novel solvents of Table I above and allowed to air dry. Upon visual inspection, the soil appears to be substantially removed.

Having described the invention in detail and by reference to preferred embodiments thereof, it will be apparent that modifications and variations are possible without departing from the scope of the invention defined in the appended claims. 

What is claimed is:
 1. A compound having the formula ##STR4## wherein R' is selected from the group consisting of CF₃ CF₂ CHF--, CF₃ CHFCF₂ --, CHF₂ (CF₂)₂ --, CF₃ CF₂ CH₂ --, CF₃ (CHF)₂ --, CF₃ CH₂ CF₂ --, CHF₂ CF₂ CHF--, CHF₂ CHFCF₂ --, CH.sub. F(CF₂)₂, CF₃ CHFCH₂ --, CF₃ CH₂ CHF--, CHF₂ CF₂ CH₂ --, CHF₂ (CHF)₂ --, CHF₂ CH₂ CF₂ --, CH₂ FCF₂ CHF--, CH₂ FCHFCF₂ --, CH₃ (CF₂)₂ --, CF₃ (CH₂)₂ --, CHF₂ CHFCH₂ --, CHF₂ CH₂ CHF--, CH₂ FCF₂ CH₂ --, CH₂ F(CHF)₂ --, CH₂ FCH₂ CF₂ --, CH₃ CF₂ CHF--, CH₃ CHFCF₂ --, CHF₂ (CH₂)₂ --, CH₂ FCHFCH₂ --, CH₂ FCH₂ CHF-- , CH₃ CF₂ CH₂ --, CH₃ (CHF)₂ --, CH₃ CH₂ CF₂ --, CH₂ F(CH₂)₂ --, and CH₃ CHFCH₂ --.
 2. 2-trifluoromethyl-1,1,1,3,4,4,5,5,5-nonafluoro-2-pentanol. 